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含查尔酮结构香豆素衍生物的合成及抗肿瘤增殖活性

刘文虎, 常晋霞, 张建武

刘文虎, 常晋霞, 张建武. 含查尔酮结构香豆素衍生物的合成及抗肿瘤增殖活性[J]. 中国药科大学学报, 2014, 45(5): 522-528. DOI: 10.11665/j.issn.1000-5048.20140503
引用本文: 刘文虎, 常晋霞, 张建武. 含查尔酮结构香豆素衍生物的合成及抗肿瘤增殖活性[J]. 中国药科大学学报, 2014, 45(5): 522-528. DOI: 10.11665/j.issn.1000-5048.20140503
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LIU Wenhu, CHANG Jinxia, ZHANG Jianwu. Synthesis and antitumor activities of novel coumarin derivatives containing chalcone moiety[J]. Journal of China Pharmaceutical University, 2014, 45(5): 522-528. DOI: 10.11665/j.issn.1000-5048.20140503
Citation: LIU Wenhu, CHANG Jinxia, ZHANG Jianwu. Synthesis and antitumor activities of novel coumarin derivatives containing chalcone moiety[J]. Journal of China Pharmaceutical University, 2014, 45(5): 522-528. DOI: 10.11665/j.issn.1000-5048.20140503
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含查尔酮结构香豆素衍生物的合成及抗肿瘤增殖活性

  • 1.

    川北医学院 药学院

  • 2.

    川北医学院 微生物学与免疫学教研室

基金项目: 四川省教育厅项目资助(No.14ZB0195)；南充市科技计划项目资助(No.13A0033)

Synthesis and antitumor activities of novel coumarin derivatives containing chalcone moiety

摘要

    摘要
  • 摘要: 基于活性亚单元拼接原理，将查尔酮分子片段拼接到香豆素结构中，设计并合成了一系列新型含查尔酮结构的香豆素衍生物；以苯乙酮和对甲基苯甲醛为原料，经克莱森-施密特缩合、溴代、环合、消除等反应制备得到24个目标化合物；化合物结构经1H NMR、ESI-MS确证。采用MTT法评价了化合物对HepG2、DU145及A549肿瘤细胞的抗增殖作用。结果表明，部分化合物对肿瘤细胞具有较好抗增殖作用，其中 Ⅰc ， Ⅱb ， Ⅱc和Ⅱd 对HepG2和A549的抗增殖作用较强，IC50分别为2.05~9.16 mol/L和3.48~10.81 mol/L，在此基础上初步探讨了此类化合物的构效关系。
    Abstract: To explore novel coumarin derivatives with more potent antitumor activity, a series of novel compounds were designed and synthesized by linking chalcone to coumarin′s framework. Starting from acetophenone and 4-methylbenzaldehyde, the target compounds were prepared through a reaction cascade, including Claisen-Schmidt, bromination, cyclization and elimination reactions affording twenty-four novel compounds whose structures were confirmed by 1H NMR and ESI-MS techniques. In vitro antitumor activities of the compounds were evaluated against HepG2, DU145 and A549 cell lines by the standard MTT assay. The results showed that some of the target compounds exhibited strong anti-proliferative activities against selected tumor cells. Compounds Ⅰc, Ⅱb, Ⅱc and Ⅱd showed excellent anti-proliferative activities against HepG2 and A549 cell lines with the IC50 values of 2. 05-9. 16 mol/L and 3. 48-10. 81 mol/L, respectively. The structure-activity relationship of novel coumarin derivatives containing chalcone moiety is also discussed.
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    • 参考文献(13)
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  • 刊出日期:  2014-10-24

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